I know I’m not the only one who assumes that everyone around except for me has their lives figured out.
Sometimes, I feel so stuck and lost that I don’t even know whether I am on the right path or whether I am true to myself.
But then, who would guarantee that the road not taken in the past would lead to a better life?
So, when I am burdened by many what if’s and the overpowering imposter syndrome, I like to be kind to myself by asking some tough questions.
Tough questions to reflect on, not any Math or Physics question.
The Power of Questions
Every breakthrough, discovery and innovation begin with a question.
And, asking yourself questions is one of the simplest and most effective habit anyone can build in the pursuit of success.
-Questions are an exploration of the possibilities that you have. When you feel stuck at a job, a simple question like, ‘What other options do I have?” can lead to new ideas and unexpected discoveries.
-Questions can help us uncover the uncomfortable truths about ourselves, our habits, our patterns. They make us see what we’ve been avoiding. It helps us challenge our excuses.
-Additionally, the act of asking questions helps us in our journey of self-discovery. You learn about your values, what makes you different, your mindset, your relationship with others and self.
-To ask yourself questions means that you care about yourself and are ready to listen to yourself. It’s an act of self-love and an acknowledgement that your experiences, emotions and inner landscapes are worth exploring.
What are tough questions and how does it help?
Tough questions are those questions that help us confront the uncomfortable truths in life.
It pushes us to reflect and face things we’d rather avoid. When life feels like an exam asking ourselves these hard-hitting questions can actually help us find the answers we really need.
Just like in an exam, avoiding the tough questions doesn’t make them disappear. They linger, waiting for us to face them. But when we do, we often realize that the struggle to answer is where the real growth happens.
All it needs is for us to be answer these uncomfortable tough questions with raw honesty. No sugarcoating. No dodging. Just plain truth.
It’s not always easy. It can reveal fears, regrets, and desires that we’ve buried. But it also helps create space for clarity and growth.
The answers may not come instantly. But once we are ready to spill out the truth, it can feel liberating. Freedom from denial. Freedom from pretending.
Tough questions help you take responsibility for your lives and assess what is it that is holding you back. Is it your habits? Is it your mindset? Is it fear? Is it the constant need for validation?
20 Tough Questions to Ask Yourself
So, in order to make it easier for you, I have a list of questions you can ask as a part of your daily journaling routine that’ll help you navigate your life with better clarity.
1. What is the one habit I know I need to break, but keep making excuses for?
You already know what it is. That’s the frustrating part. But facing it head-on is the first step.
2. If I suddenly lost everything I rely on for security, what skills or traits would I regret not having developed?
Comfort can make us complacent. What’s one thing you could work on now to feel more prepared?
Honestly, this question makes me feel vulnerable. It nudges me to not take things for granted and instead keep investing in my personal growth.
2020 was a challenging time for thousands of people globally and it reminded us how fragile stability can be. So, if another unexpected challenge came, what would you wish you had already strengthened?
Also read: What to do When you Feel Disappointed and Discouraged in Life
3. What is one belief I hold about myself that is actually holding me back?
Sometimes, we tell ourselves stories that aren’t true. What if you challenged that belief? What if the thing holding you back isn’t my circumstances, but the way you see myself?
Maybe you believe you’re not good enough. Perhaps you tell yourself you’re not ready yet. Maybe you think success is for other people, not you. These beliefs feel real because you’ve repeated them so many times. But are they actually true?
What if you asked, What if I am good enough? What if I am ready?
Here is a positive self-talk guide that might be helpful.
4. If I had to justify every hour of my day to someone I deeply respect, what would I be most ashamed of?
Where is your time really going?
Are you mistaking busyness for productive? Are you just occupied by tasks that isn’t really important?
Maybe you’re drowning in your to-do lists and not feeling accomplished. Or, are you stuck in cycles of procrastination and mindless scrolling and failing to spend time intentionally?
These tough questions may make you feel guilty but you also gain awareness of how you’re spending your time.
5. Who in my life makes me feel small or incapable, and why do I still let them influence me?
Just because you’ve tolerated it doesn’t mean you have to keep doing so.
It might be someone close to you, a family member, a friend, or even a partner who constantly belittles you. Or maybe it’s someone you admire, whose opinions you’ve taken as truth, even when they make you doubt yourself.
6. If my life had a narrator who was completely honest, what harsh truth would they reveal about my daily choices?
Imagine hearing your own life story aloud. Would you be proud, or would you cringe?
This question can also reveal what you think about yourself. It gives a chance to step outside ourselves and listen.
I can think of what my narrator would say about my present life situation: This girl has dreams and potential but is stuck in the in-between phase where uncertainty looms large.
7. What am I pretending not to know about my own patterns and behaviors?
We all have blind spots. What’s one truth you’ve been avoiding?
“I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy to finishing the only work that mattered to me.”- J.K Rowling
Rowling’s realization helped her stop making excuses and fully commit to writing, despite the hardships she faced. What would happen if you stopped pretending? If you acknowledged the habits, fears, or excuses that hold you back?
8. If I continue making decisions the way I have in the past year, what is the most likely outcome for my life?
This is a reality check for you to reflect on.
It’s about being intentional with your life choices rather than being overly critical of your past choices. Be it taking a job or a hobby or purchasing things or delaying something.
9. What goal have I convinced myself is “impossible” when it’s really just uncomfortable or inconvenient?
Hard isn’t the same as impossible.
Maybe I’ve convinced myself that I can’t switch careers, when really, I just don’t want to start from scratch. Or, maybe I tell myself I don’t have time to write that book, when in reality, I just haven’t made it a priority. Maybe I believe I can’t be consistent with healthy habits, when the truth is, I just don’t like the discomfort of discipline.
10. If someone followed me around for a week and copied everything I did, would their life improve or deteriorate?
Now, that’s something to think about.
11. What am I clinging to out of fear, rather than genuine desire or necessity?
Not everything we hold onto is worth keeping. But, letting go is also a process.
Ask yourself how to make it easier to let go.
12. If I could see myself from an outsider’s perspective, what advice would I give?
It’s easier to be wise for others. But what if you took your own advice?
13. What is one thing I regularly complain about but haven’t actually done anything to fix?
Complaints without action are just noise. What’s one small step you could take?
14. What’s one thing you keep saying you’ll do “someday”—and what would it take for you to start today?
“Someday” is a lie we tell ourselves to feel better about inaction. What’s something you keep postponing because it feels too big, too scary, or too uncertain? What if you took one tiny step toward it now?
15. If my younger self/older self-saw my current daily habits, what would they think?
Would they be impressed? Disappointed? Inspired?
16. What is one difficult conversation I am avoiding that would significantly improve my life if I had it?
Avoidance doesn’t make things easier—just delayed. Maybe it’s time.
17. If you suddenly had to start over tomorrow with nothing but your mind and experiences, what’s the first thing you’d do?
No job, no relationships, no comfort zones. Just you, starting fresh. What would you rebuild first? And what does that say about what truly matters to you?
I often ask myself this question and I feel relieved when I find answers.
18. Where am I making my life harder than it needs to be because I refuse to ask for help or let go?
Sometimes, struggle is a choice. What would happen if you let yourself receive support?
19. What is your best quality, and do you allow yourself to fully embrace it or do you downplay it?
It’s easy to acknowledge flaws, but what about your strengths? Do you truly own them, or do you brush them off, thinking, It’s not a big deal?
Imagine if you leaned into your best quality unapologetically. How would that change the way you live?
20. How have you truly shown up for yourself lately—not just in responsibilities, but in care and self-compassion?
We often measure our worth by how well we show up for others.
But what about ourselves? Have you given yourself patience, kindness, and space to rest? Or have you been neglecting your own needs while keeping up with obligations?
What’s one small way you can genuinely show up for yourself today?
Self-reflection is powerful when you’re willing to face the truth and make changes.
All you need is a journal where you can sit with your thoughts and question and be brutally honest with it.
As I always say, asking questions is the first step towards creating lasting change.
Your answers today may be different from your answers a year from now. Growth isn’t static. Revisiting tough questions allows you to track your progress and see how your mindset evolves.
More on Self-reflection
- 35 Journal Prompts for Meaningful Self-Reflection
- Questions to Help you Know Yourself Better
- Gratitude Journal Prompts for your Night Routine
